55474-17-4

Usage

Appearance

White to off-white powder.

Solubility

Soluble in water.

Classification

Synthetic derivative of glucose.

Use as a protective group

Commonly used in carbohydrate chemistry.

Use as a reagent

For the synthesis of various glycosides.

Application in preparation

Employed in the preparation of thioglycosides and other glycosidic derivatives.

Functional groups

Acetyl groups and thiol functionality.

Versatility

Serves as a versatile building block for the synthesis of complex organic compounds.

Upstream product

• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 

Downstream Products

• 102527-08-2 S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->1)-(2R,3R,4E)-3-benzoyloxy-2-octadecanamido-4-octadecene-1-thiol 
• 136591-19-0 Benzoic acid (E)-(R)-1-[(R)-1-amino-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl]-hexadec-2-enyl ester 

Relevant academic research and scientific papers

A general strategy toward S-linked glycopeptides

(Chemical Equation Presented) A high-yield one-pot synthesis of S-linked glycosyl amino acids 1 has been developed (see scheme; DMF = dimethyl formamide) and used in the solid-phase synthesis of S-linked glycopeptides. This approach has been shown to be efficient for the synthesis of various S-linked glycosyl amino acid building blocks.

Synthesis of cerebroside, lactosyl ceramide, and ganglioside GM3 analogs containing β-thioglycosidically linked ceramide

Coupling of the sodium salt of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose, -β-D-galactopyranose, O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O- acetyl-1-thio-β-D-glucopyranose, or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto -2-nonulopyranosylonate)-(2→3)-O-(2,3-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-3-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D- glucopyranose, which were prepared from the corresponding 1-S-acetates, 1, 3, 6, and 9, with (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene- 1,3-diol (12) derived by tosylation of 11, gave the corresponding β-thioglycosides 13, 17, 21, and 25, respectively in good yield. The β-thioglycosides obtained were converted, via selective reduction of the azide group, condensation with octadecanoic acid, and removal of the protecting groups, into the title compounds. Coupling of the sodium salt of 2,3,4,6-tetra-O- acetyl-1-thio-β-D-glucopyranose, -β-D-galactopyranose, O-(2,3,4,6-tetra- O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3, 6-tri-O-acetyl-1-thio- β-D-glucopyranose, or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3, 5-dideoxy-D-glycero-α- D-galacto-2-nonulopyranosyl-onate)-(2→3) -O-(2,3-di-O-acetyl -6-O-bezoyl-β-D-galactopyranosyl) -(1→4) -3-O-acetyl-2,6-di-O- benzoyl-1-thio-β-D-glucopyranose, which were prepared from the corresponding 1-S-acetates, 1, 3, 6, and 9, with ( 2S,3R,4E)-2-azido-3 -O-benzoyl-1-O-(p-tolylsulfonyl) -4-octadecene-1,3 -diol (12) derived by tosylation of 11, gave the corresponding β-thioglycosides 13, 17, 21, and 25, respectively in good yield. The β-thioglycosides obtained were converted, via selective reduction of the azide group, condensation with octadecanoic acid, and removal of the protecting groups, into the title compounds.